Green substantive trisazo dyes.



JENS DEDICHEN, F BERILIN'HALENSEE, AND WERNER BANGLE, 0F BERIJNJRm-lDENAU, GERMANY, ASSIG'NORS 'IC) AGTIEN GESELLSCHAFI. F'fi'R i TION, 0FBEBLHI; GERMANY.

GREEN SUBSTANTIVE TRTESAZO EYES.

1183,8381. No Drawing.

1 '0 a whom it may concern:

Be it known that we, Jams DEDIOHEN and.

WERNER LANGE, the formera citizen of Norway and the latter a citizen ofGermany,

residing at Berlin-Halensee, Germany, and

Berlin-Friedenain Germany, our post-office addresses beingSeesenerstrasse 25, Berlina nyl-3-methyl-5-pyrazolonefiji Halensee,Germany, and Feurigstrasse 10,

R OH

Specification of Letters Patent.

trisazo-dyes dyeing cotton green.

certain new and useful Improvementsjjn a: I.- FABRIKA Patented May 16;teas,

Application filed June 5, saris. Serial n6. sans.

Green Substantive Trisazo 'Dyes of which" the following isaspecification. y

The present invention relates to new These dyes correspond to thegeneral formula;

v 3 am y R meaning a univalent atom or radical,

diazotizing the et-amindazo-compound prepared from 'adiazonaphthaleneesulfonic acid and an'a'mino-compound of the naphthaleneseries and combining the diazocompound with a 1-aminobenzoylamino-S-naphtliol-sulfonic acid, further diazotizing the disazo-compound and,coupling at last with a pyra'zolone-derivative, such as l-phe- The newdyes are in to shape of their dry sodium salts blackish powders solublein water with green color not being essentially alteredby soda-lye. Theaddition of hydrochloric acid to the neutral solution causes a greenprecipitation. Concentrated sulfuric acid dissolves the dyes to a greensolution from which the dyes are precipitated by addition of icee Thedyes, produc ing on cotton green shades, are destroyed by strongreducing agents, the solution becoming colorless. The products ofreduction are a naphthylamin sulfonic acid, a para diamin of thenaphthalene series, a l-ammo benzoylamino 7 amino-8-naphthol-sulfonicNaOzQ equivalents can; hesubstituted acid and a 4amino-1-ary-5-pyrazolone, such, asi-amm'o-1-phenyl-3-methyl-5-pyrazolone.

The followingexample serves-the parts being by weight-4:0 illustrate theinvention without limiting it 32.5 parts of 2-naphthylamm-4.8-disulfonic acid (monosodium salt) are diazotized withparts of sodium I1lt11t8 1n hydrochloric acid. The .'diazo-- compound iscombined with 15 parts of 1-- naphthylamin. Then 7 .5 parts of sodiumnitrite dissolved in water are added. The

diazoazocompound formed is salted out filtered off, suspended in water,mixed with a cooled solution of 30.5 aminobenzoylamino 8-naphthol 4.sulfonic acid alkaline by sodium carbonate. The

combination being complete the blue disaz0-" dye is salted out in theheat,-then dissolved in Water and diazotized at ordinary temperaturewith 7 parts of sodium nitrite and hy-- drochloric acid. Thediazo-disazo-compound in combined with 17 .5 parts of*1'-phenyl-3-lmethyl-fi-pyrazolonein the presenceof so dium carbonate; The dye issalted out, drained anddried. "It probably corresponds to the formula: ii

mil-.0- i sheaf O Na parts of l-metafor instan e.

1 aminobenzoylanund8-naphthol-ksulfonic acid may be replaced by-1-metaor 1- araaminobenzoylamino 8 naphthol 3.6 ulfonic acid and thel-naphthylamin by amino-2-naphthol-ethyl ether or. a sulfonic acid ofone of these compounds.

which on addition of ice the dye is precipitated; being destroyed bystrong reducing agents yielding 2-naphthylan in-4.8 disu1- rived from a'naphthylamin-sulifonic acid, an

amino-compound of the naphthalene series, a 1 aminobenzoylamino 8naphthol sulamino-S-naphthol-sulfonic acid and -1- phenyl 3 methyl 5pyrazolone and corresponding to the formula:

We claim, tonic acid and a pyrazolone-derivative and 5 1. Theherein-described trisaZo-dyes decorresponding to the general'formular 1R meaning a univalent atom or radical, yieldingm naphthylamin sulfonicacid, a such as hydrogen, an alkoxyor a sulfonic para-diamin of thenaphthalene series, a group: as sodium salts being blackish pow- 1annnobenzoyl amino 7 amino 8 naphders, soluble in water with greencolor, not thol-sulfonic acid and a 4-ammo-1-aryl-5- 15 essentiallyalterable by soda lye; from pyrazolone. v y

aqueous solution dyeing cotton green; the 2. The herein-describedtriszizo-dyes tiedye being precipitated in green flocks from rived froma naphthylamln-sulfonic acid, the solution by addition of hydrochloric lnaphthylainin, a 1 -an1inobenzoylamino- 8Q acid; being dissolyed by'concentrated 5111- 8 naphthol sulfonic acid and 1 aryl 3 furic acid to agreen solution, from which niethyl-fi pyrazolone and corresponding to onaddition of ice, the dye is precipitated; the general formul beingdestroyed by strong reducing agents c1uH1-;N=N- N=N-C1uH5NH.CO.C5Hr-N=N-CH v son!)x scan i as sodium salts being blackish powderssoluthylamin snlfonic acid, lA-diaminonaph- J5 ble in Water with greencolor not essentially thalene, a 1-aminobenzoylamino-7-aminoalterable bysoda lye, from aqueous solutions S-naphtholsulfonic acid and 4-amino-1-dyeing cotton green; the dye being precipiaryl-23-1nethyl 5-pyrazolone.1

tated in green flocks from the solution by 3. The herein-describedtrisazo-dyes deaddition of hydrochloric acid; being disrived from2-naphthylamin-4.8-disulfonic l0 solved by concentrated sulfuric acid toa acid, I-naphthylamin, a l-amino-benzoylgreen solution, fronrwhich onaddition of arnino-S-naphtholsu]fonio acid and l-arylice the dye isprecipitated; being destroyed 3-niethyl-5-pyrazolone and correspondingto by strong reducing agents yielding a-naphthe formula: v

. Boas r' 03 :m

Vu=n N=NdwH5. NH.C0.C H4N=NCH I i s omv OI--u.ryl;

OaH i as sodium salts being blackish powders,'solufonic acid, 1.4diamino naphthalene, a ble in Water with green color not essentially 1 raminobenzoylamino 7 amino 8- 66 alterable by soda-lye; dyeing cottongreen; naphthol-sultonic acid and 4-amino1-arvlthe dye beingprecipitated in green flocks 3-Inethyl-5-pyrazolonel from the solutionby addition of hydro-. 4. The herein-described trisazo dyes de chloricacid; being dissolved by concenrived from Z-naphthvla1nin-4.8-disultonictrated sulfuric acid to a green solution, from acid, l-naphthylamin, a1-ai;nino-benz0yl- 70 I as sodium salts being blackish powderssolualterable by soda lye; dyeing cotton green; 15 ble 1n water withgreen color, not essentially the dye being precipitated in green flocksfrom'the. solution bythe addition of hydrochloric acid,being dissolvedby concentrated v sulfuricaeid to a green solution from which onaddition of ice the dye is precipitated;

being,destroyed by strong reducing agents yieldingQ-naphthylam'in-4.8'-disulfonic acid, 1.4 diaminonaphthalene, a 1 aminobenzoyla1nino-7-amino-S-naphthol-sulfonic acid as sodium salt being ablackish power, soluble in water with green color not essentially beingdestroyed. by strong reducing agents yielding2-naphthy1amin-4.8-disulfonic acid,

1-4-dia1ninonaphthalene, l-meta-aminobenand4-amino-1-phenyl-3-1nethy1-5-pyrazolone.

5. The herein-described trisazodye derived from2-naphthylamin-4.8-disulfonic acid, l-naphthylamin, l'rneta-aminobenzoylamino-8-naphthol-4-sulfonic acid and. 1-

pheny1-3-methyl-5-pyrazolone and corre-- sponding to the formula:

zoylamino 7 amino 8 naphthol 4 sul- 'fonic acid and 4-amino-1-phenyl-3methyl- 5-pyraz0lone. V

In testimon whereof We have hereunto set our hands in presence of twosubscribing witnesses.

r JENS DEDICHEN. WERNER LANGE. Witnesses:

Hminr HAsPER, WOLDEM AR HAUPT.

